NL8105326A - Xanthaten. - Google Patents
Xanthaten. Download PDFInfo
- Publication number
- NL8105326A NL8105326A NL8105326A NL8105326A NL8105326A NL 8105326 A NL8105326 A NL 8105326A NL 8105326 A NL8105326 A NL 8105326A NL 8105326 A NL8105326 A NL 8105326A NL 8105326 A NL8105326 A NL 8105326A
- Authority
- NL
- Netherlands
- Prior art keywords
- xanthate
- alkali metal
- group
- sodium
- potassium
- Prior art date
Links
- 239000012991 xanthate Substances 0.000 title claims description 34
- -1 tricyclodecyl Chemical group 0.000 claims description 36
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims description 33
- 239000011734 sodium Substances 0.000 claims description 25
- ZOOODBUHSVUZEM-UHFFFAOYSA-N ethoxymethanedithioic acid Chemical compound CCOC(S)=S ZOOODBUHSVUZEM-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 21
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 20
- 229910052783 alkali metal Inorganic materials 0.000 claims description 20
- 229910052700 potassium Inorganic materials 0.000 claims description 20
- 239000011591 potassium Substances 0.000 claims description 20
- 229910052708 sodium Inorganic materials 0.000 claims description 20
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 19
- 150000001340 alkali metals Chemical group 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 230000001790 virustatic effect Effects 0.000 claims description 7
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- KMJJWVCLFJXUQF-UHFFFAOYSA-M sodium;cyclohexyloxymethanedithioate Chemical compound [Na+].[S-]C(=S)OC1CCCCC1 KMJJWVCLFJXUQF-UHFFFAOYSA-M 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
- OPLBMJFYACKMRJ-UHFFFAOYSA-N o-cyclohexyl methylsulfanylmethanethioate Chemical compound CSC(=S)OC1CCCCC1 OPLBMJFYACKMRJ-UHFFFAOYSA-N 0.000 claims description 3
- WIKDURKPSJEWGB-UHFFFAOYSA-N phenylmethoxymethanedithioic acid Chemical compound SC(=S)OCC1=CC=CC=C1 WIKDURKPSJEWGB-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 claims description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- QMPPYLFXRKUTOR-UHFFFAOYSA-N decoxymethanedithioic acid Chemical compound CCCCCCCCCCOC(S)=S QMPPYLFXRKUTOR-UHFFFAOYSA-N 0.000 claims 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- WKMBNCWYZBDIEA-UHFFFAOYSA-N heptoxymethanedithioic acid Chemical compound CCCCCCCOC(S)=S WKMBNCWYZBDIEA-UHFFFAOYSA-N 0.000 claims 1
- JZGDVCTYNFVQEC-UHFFFAOYSA-M potassium;adamantane-1-carboxylate Chemical compound [K+].C1C(C2)CC3CC2CC1(C(=O)[O-])C3 JZGDVCTYNFVQEC-UHFFFAOYSA-M 0.000 claims 1
- GBBPFRKNGUDLLB-UHFFFAOYSA-M sodium;cyclododecanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCCCCCCCC1 GBBPFRKNGUDLLB-UHFFFAOYSA-M 0.000 claims 1
- XTIVBOWLUYDHKE-UHFFFAOYSA-M sodium;cyclohexanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCC1 XTIVBOWLUYDHKE-UHFFFAOYSA-M 0.000 claims 1
- LFQULJPVXNYWAG-UHFFFAOYSA-N sodium;phenylmethanolate Chemical compound [Na]OCC1=CC=CC=C1 LFQULJPVXNYWAG-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 14
- 241000700605 Viruses Species 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000000921 elemental analysis Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 206010022000 influenza Diseases 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical class C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000428 dust Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 229910052573 porcelain Inorganic materials 0.000 description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 229960005486 vaccine Drugs 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 241001529453 unidentified herpesvirus Species 0.000 description 2
- ZQTYQMYDIHMKQB-DSYKOEDSSA-N (1r,3r,4s)-bicyclo[2.2.1]heptan-3-ol Chemical compound C1C[C@@H]2[C@H](O)C[C@H]1C2 ZQTYQMYDIHMKQB-DSYKOEDSSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- HIPPBUJQSIICJN-UHFFFAOYSA-N 3385-61-3 Chemical compound C12CC=CC2C2CC(O)C1C2 HIPPBUJQSIICJN-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 235000006491 Acacia senegal Nutrition 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 229920002261 Corn starch Polymers 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
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- VLLNJDMHDJRNFK-UHFFFAOYSA-N adamantan-1-ol Chemical compound C1C(C2)CC3CC2CC1(O)C3 VLLNJDMHDJRNFK-UHFFFAOYSA-N 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- WOLHOYHSEKDWQH-UHFFFAOYSA-N amantadine hydrochloride Chemical compound [Cl-].C1C(C2)CC3CC2CC1([NH3+])C3 WOLHOYHSEKDWQH-UHFFFAOYSA-N 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
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- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QGJOPFRUJISHPQ-NJFSPNSNSA-N carbon disulfide-14c Chemical compound S=[14C]=S QGJOPFRUJISHPQ-NJFSPNSNSA-N 0.000 description 1
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- SFVWPXMPRCIVOK-UHFFFAOYSA-N cyclododecanol Chemical compound OC1CCCCCCCCCCC1 SFVWPXMPRCIVOK-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 210000003800 pharynx Anatomy 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
- C07C329/02—Monothiocarbonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/265—Esters, e.g. nitroglycerine, selenocyanates of carbonic, thiocarbonic, or thiocarboxylic acids, e.g. thioacetic acid, xanthogenic acid, trithiocarbonic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3044525 | 1980-11-26 | ||
| DE3044525 | 1980-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8105326A true NL8105326A (nl) | 1982-06-16 |
Family
ID=6117628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8105326A NL8105326A (nl) | 1980-11-26 | 1981-11-25 | Xanthaten. |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US4602037A (el) |
| JP (2) | JPS5943944B2 (el) |
| KR (1) | KR870001238B1 (el) |
| AR (1) | AR230264A1 (el) |
| AT (1) | AT376202B (el) |
| AU (1) | AU549653B2 (el) |
| BE (1) | BE891245A (el) |
| CA (1) | CA1175047A (el) |
| CH (1) | CH651546A5 (el) |
| DE (1) | DE3146772C2 (el) |
| DK (1) | DK170068B1 (el) |
| ES (1) | ES8400398A1 (el) |
| FR (1) | FR2494689B1 (el) |
| GB (1) | GB2091244B (el) |
| GR (1) | GR76308B (el) |
| HU (1) | HU187476B (el) |
| IE (1) | IE51944B1 (el) |
| IT (1) | IT1195297B (el) |
| LU (1) | LU83795A1 (el) |
| NL (1) | NL8105326A (el) |
| PL (1) | PL129383B1 (el) |
| SE (1) | SE450251B (el) |
| SG (1) | SG29285G (el) |
| YU (1) | YU42120B (el) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR870001238B1 (ko) * | 1980-11-26 | 1987-06-26 | 메르츠+캄패니 게엠베하 앤드 캄패니 | 크산틴산염의 제조방법 |
| PT83127B (pt) * | 1985-08-02 | 1989-03-30 | Merz & Co | Processo para a preparacao de novas composicoes farmaceuticas contendo um xantano de accao antiviral e antitumoral |
| DE3625948A1 (de) * | 1985-08-02 | 1987-02-19 | Merz & Co Gmbh & Co | Antivirale und antitumor-zusammensetzung, verfahren zu deren herstellung und deren verwendung |
| IT1213453B (it) * | 1985-08-02 | 1989-12-20 | Merz & Co Gmbh & Co | Composizione farmaceutica. |
| US5055296A (en) * | 1988-08-04 | 1991-10-08 | Wagle Sudhakar S | Method of treating chronic fatigue syndrome |
| US5316775A (en) * | 1988-08-04 | 1994-05-31 | Kremers-Urban Company | Method of treating hepatitis B infection |
| US5334395A (en) * | 1988-08-04 | 1994-08-02 | Kremers-Urban Company | Method of treating an epstein-barr viral infection |
| US5284664A (en) * | 1988-08-04 | 1994-02-08 | Kremers-Urban Company | Method of treating the symptoms of Alzheimer's disease |
| EP0450492A1 (en) * | 1990-04-06 | 1991-10-09 | Tosoh Corporation | Alkylxanthate, production thereof, photopolymerization initiator, and polymerization employing the same |
| AU4159596A (en) * | 1994-11-14 | 1996-06-06 | Ct-Holding Sa | Antiviral and antitumor pharmaceutical compositions |
| DE10117728A1 (de) * | 2001-04-09 | 2002-10-17 | Biosphings Ag | Pharmazeutische Formulierungen für Xanthogenate |
| DE10156617A1 (de) * | 2001-11-17 | 2003-05-28 | Biosphings Ag | Herstellung reiner Stereoisomere von Tricyclo[5.2.1.0··2··.··6··]-dec-9-yl-xanthogenat und Arzneimittel daraus |
| EP1391221A1 (en) * | 2002-08-23 | 2004-02-25 | Deutsches Krebsforschungszentrum Stiftung des öffentlichen Rechts | A pharmaceutical preparation containing palladium complex compounds and the uses thereof for treating cancer and autoimmune disease |
| DE10343365A1 (de) * | 2003-09-17 | 2005-04-14 | Biosphings Ag | Pharmazeutische Formulierungen von Xanthogenaten und Hemmstoffen der viralen Nukleinsäurereplikation |
| DE102005031265A1 (de) * | 2005-07-05 | 2007-01-18 | Sms Demag Ag | Spreizbarer Haspeldorn |
| DE102006014390A1 (de) | 2006-03-29 | 2007-10-04 | Biosphings Ag | Assoziate von Xanthogenaten mit Cyclodextrinen und ihre Verwendung |
| MX2010000120A (es) * | 2007-07-03 | 2010-04-21 | Lumavita Ag | Estereoisomeros de triciclodecan-9-il-xantogenato. |
| KR101617055B1 (ko) * | 2008-07-15 | 2016-04-29 | 바스프 에스이 | 디알킬 설파이드의 정제 방법 |
| US20100221809A1 (en) * | 2008-12-23 | 2010-09-02 | The Regents Of The University Of California | Compositions and Methods for the Isolation of Biologically Active Proteins |
| CN114478339B (zh) * | 2022-02-14 | 2023-12-08 | 中南大学 | 一种黄原酸盐类捕收剂的制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1854525A (en) * | 1929-11-11 | 1932-04-19 | Shell Dev | Tertiary xanthates |
| US1886587A (en) * | 1930-01-09 | 1932-11-08 | Hercules Powder Co Ltd | Method of preparing xanthates of terpene alcohols |
| US2037718A (en) * | 1932-11-09 | 1936-04-21 | Du Pont | Xanthates and method of making same |
| US2037717A (en) * | 1932-11-09 | 1936-04-21 | Du Pont | Xanthates and method of making same |
| FR790353A (fr) * | 1934-05-22 | 1935-11-20 | Bataafsche Petroleum | Préparation de xanthates |
| US2161584A (en) * | 1936-08-01 | 1939-06-06 | Socony Vacuum Oil Co Inc | Petroleum lubricant composition |
| US2811432A (en) * | 1953-07-17 | 1957-10-29 | Monsanto Chemicals | Herbicidal composition |
| US3864469A (en) * | 1967-12-16 | 1975-02-04 | Hoechst Ag | Xanthines in pharmaceutical preparations and for stabilization of vitamins |
| US3864417A (en) * | 1970-01-16 | 1975-02-04 | Chevron Res | Saturated hydrocarbon disproportionation at low temperatures |
| ZA715615B (en) * | 1970-10-05 | 1972-04-26 | American Cyanamid Co | Manufacture of alkali metal xanthates |
| US3965137A (en) * | 1974-05-02 | 1976-06-22 | Stauffer Chemical Company | Thiocyano xanthates |
| KR870001238B1 (ko) * | 1980-11-26 | 1987-06-26 | 메르츠+캄패니 게엠베하 앤드 캄패니 | 크산틴산염의 제조방법 |
-
1981
- 1981-11-24 KR KR1019810004542A patent/KR870001238B1/ko active
- 1981-11-24 DK DK522081A patent/DK170068B1/da not_active IP Right Cessation
- 1981-11-24 AR AR287572A patent/AR230264A1/es active
- 1981-11-25 FR FR8122055A patent/FR2494689B1/fr not_active Expired
- 1981-11-25 PL PL1981233966A patent/PL129383B1/pl unknown
- 1981-11-25 NL NL8105326A patent/NL8105326A/nl not_active Application Discontinuation
- 1981-11-25 SE SE8107022A patent/SE450251B/sv not_active IP Right Cessation
- 1981-11-25 CA CA000390861A patent/CA1175047A/en not_active Expired
- 1981-11-25 ES ES507430A patent/ES8400398A1/es not_active Expired
- 1981-11-25 HU HU813521A patent/HU187476B/hu not_active IP Right Cessation
- 1981-11-25 DE DE3146772A patent/DE3146772C2/de not_active Expired - Fee Related
- 1981-11-25 GB GB8135536A patent/GB2091244B/en not_active Expired
- 1981-11-25 BE BE0/206650A patent/BE891245A/fr not_active IP Right Cessation
- 1981-11-25 IE IE2768/81A patent/IE51944B1/en not_active IP Right Cessation
- 1981-11-26 AT AT0510181A patent/AT376202B/de not_active IP Right Cessation
- 1981-11-26 GR GR66624A patent/GR76308B/el unknown
- 1981-11-26 IT IT25291/81A patent/IT1195297B/it active
- 1981-11-26 CH CH7576/81A patent/CH651546A5/de not_active IP Right Cessation
- 1981-11-26 LU LU83795A patent/LU83795A1/fr unknown
- 1981-11-26 AU AU77928/81A patent/AU549653B2/en not_active Ceased
- 1981-11-26 YU YU2782/81A patent/YU42120B/xx unknown
- 1981-11-26 JP JP56188502A patent/JPS5943944B2/ja not_active Expired
-
1983
- 1983-05-13 US US06/494,393 patent/US4602037A/en not_active Expired - Fee Related
- 1983-05-24 JP JP58091411A patent/JPS591416A/ja active Granted
-
1985
- 1985-04-22 SG SG292/85A patent/SG29285G/en unknown
-
1989
- 1989-12-29 US US07/458,889 patent/US4981869A/en not_active Expired - Fee Related
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| BT | A notification was added to the application dossier and made available to the public | ||
| A85 | Still pending on 85-01-01 | ||
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| CNR | Transfer of rights (patent application after its laying open for public inspection) |
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